Are you hitting the 50s milestone? There’s no reason that you should let your fashion sense fall to the wayside. As a matter of fact, it’s your time to perk up your dressing game. It is your time to dress sleeker than you ever had. With your spiked up confidence level at this age, your wardrobe should depict and manifest how seasoned and esteemed you are. Nearing it myself, my HughesNet plans have never come in handy than now. On a hot Sunday afternoon, my favorite pastime is searching the entire web for looks to try on. You should too!

Enjoy your sixth decade with style. And don’t be reluctant to experiment all the clever dressing hacks to look your best! Here is some useful and awesome style advice.

Top 10 Subtle Dressing Tips to Look Timelessly Stylish

  1. Wear Small Prints
  2. Go for Subtle Branding
  3. Flaunt the Sophistication of a Pocket Square
  4. Embrace the Glasses
  5. Keep the Heels to the Minimum
  6. Build Up a Tie Repertoire
  7. Say No to Anything “Distressed” or Ripped
  8. Balance the Patterns Out with Solid Color
  9. Invest in Flattering and Tailored Coats
  10. Shine Your Shoes, Actually!

Ready to shine? Let’s do it!

Wear Small Prints


Ladies, it’s time to quit wearing bold and large patterns. Large prints can now be your downfall. Choose smaller prints. And don’t wear them as dresses which go head-to-toe. If worn well, they can do wonders to make your body look slimmer. They can also serve the purpose of adding class and boldness. It’s a good idea to come up with a mix and match of small prints and solid colors.

Go for Subtle Branding

As you are in your 50s, we assume that now you can afford to shop from expensive brands. But indulging in pricey brands doesn’t mean that you are going to flaunt them in an obvious manner. Pick stuff with subtle branding. Huge logos and printed words are a no-no. Pick pieces, which have subtle branding. Scrutinize them thoroughly before you buy them.

Flaunt the Sophistication of a Pocket Square

Gentlemen, haven’t you been waiting for the time in your life when you were mature enough to pull off a nice pocket square? Well, you are there now! Consider having a collection of plain and patterned pocket squares to add to your dinner jackets.

A nicely wrapped pocket square signifies class and style, especially when you wear to a date. Now that you have aged like the aging of fine wine, this is the best time to be sophisticated. If you are currently dating, consider pocket square a must-have accessory to look great in a suit. Pair it with a vintage wristwatch and you are all set!

Embrace the Glasses


You may have been made fun of in your teens for wearing glasses. But guess what! In your 50s, glasses are officially going to be your favorite accessory. It adds the element of grace, elegance, and wisdom. And that’s true for both men and women of that age. Just like you have embraced your natural features at this age, embrace your glasses too.

Keep the Heels to the Minimum

Ladies, if you love heels, you must have worn them enough by this age. When you hit your 50s, high heels can cause bad posture behavior. Now that your bones are getting tender and comfort has to be your top priority, you need to stop wearing high heels. Instead, choose age-appropriate heels to keep your overall look stylish.

Build Up a Tie Repertoire

Have you ditched the novelty tie? Are you still managing your formal dressing with a bunch of ties? If yes, now is the time to own a collection of ties. Collect ties of all kinds. You should own knitted, wool, and silk ties. They should be staples in your wardrobe. Own a few bow ties too. You need all these accessories now to make your suits look perfect. Wearing the right tie to a perfect formal date is the best thing that you can do to yourself.

Say No to Anything “Distressed” or Ripped

It’s time to say goodbye to all the juvenile fashions. You need to take them out of your wardrobe right away. This essentially includes distressed and ripped jeans and everything else that falls in the same category. You need to look your age and that demands to stick to age-appropriate clothing. Especially on dates, never wear ripped jeans.

Balance the Patterns Out with Solid Color

We have established already that bold and large prints can look cheap and tawdry on you. you need to keep things classic and age-appropriate. So, keep the patterns smaller. To add more class, contrast them with solid colors. For instance, wear a long coat of a solid color and a top with a pattern. Just make sure you don’t look too overwhelming.

Invest in Flattering and Tailored Coats

Gentlemen, outerwear has to be flattering. Now that you can invest in your wardrobe, go for sleek and tailored jackets and coats. Scrutinize your wardrobe thoroughly this weekend. And donate everything that is overly furry, bulky, or frumpy. Also, be wary of buying cheap denim.

Now that you are not young, your body is not firm and tight like before. So, poorly-made and inexpensive denim is not easy to get away with. Go for a pair of bootleg jeans. It will lengthen the legs and will make your tummy flatter.

Shine Your Shoes, Actually!

Whether you pay someone for doing it or do it yourself, make sure your loafers and shoes shine to perfection. In your 50s, sporting dull shoes is a major put-off. Especially on dates. You just shouldn’t wear dull shoes!

Last but not least, and perhaps the most important piece of advice. You need to be comfortable in your skin and with your age. The style advice is not intended to hide your history behind your dresses or looks. It is not intended to make you look 25. It is only to make you look stylish at YOUR age.

One good way to find your style is to look online. That helps a lot. At least it did for me when I was traveling. I still remember how clueless I was about where to go for shopping a few formal clothing items for my dinner date. To make it worse, I had no access to the internet.

Then someone referred me to Hughesnet customer service. Being on a budget, that was a life-saver! After getting a nice package, I browsed a few online stores and finally found what I was looking for.  It was not too formal yet quite elegant.  And suitable for my age.

The idea is to work on keeping yourself on top of the style game while staying true to your age. Good luck!